Borylated norbornadiene derivatives: Synthesis and application in Pd-catalyzed Suzuki–Miyaura coupling reactions

• Robin Schulte and
• Heiko Ihmels

Beilstein J. Org. Chem. 2022, 18, 368–373, doi:10.3762/bjoc.18.41

• quadricyclane upon irradiation, whereas the back reaction can be accomplished by thermal treatment. Keywords: molecular solar thermal system; Pd-mediated catalysis; photochemistry; photoswitches; quadricyclanes; Introduction Norbornadiene (1a, bicyclo[2.2.1]heptadiene) is a photochromic compound that has

Experimental and computational electrochemistry of quinazolinespirohexadienone molecular switches – differential electrochromic vs photochromic behavior

• Eric W. Webb,
• Jonathan P. Moerdyk,
• Kyndra B. Sluiter,
• Benjamin J. Pollock,
• Amy L. Speelman,
• Eugene J. Lynch,
• William F. Polik and
• Jason G. Gillmore

Beilstein J. Org. Chem. 2019, 15, 2473–2485, doi:10.3762/bjoc.15.240

• as photooxidants, the difference in the reduction potential between LW and SW would need to be increased further, and LW would need to be more reducible to be of use in photooxidation of relevant substrates (e.g., Dewar benzenes, quadricyclanes, or bishomocubanes as quantum amplified isomerization

Norbornadiene-functionalized triazatriangulenium and trioxatriangulenium platforms

• Roland Löw,
• Talina Rusch,
• Tobias Moje,
• Fynn Röhricht,
• Olaf M. Magnussen and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1815–1821, doi:10.3762/bjoc.15.175

• (NBD) and quadricyclanes (QC) attached to TATA and TOTA platforms which can be used to check if these accelerated rates and the spin change mechanism also apply to [2 + 2] cycloreversions (QC→NBD). Keywords: [2 + 2] cycloaddition; [2 + 2] cycloreversion; norbornadiene; photochemical isomerization

• photostationary state of NBD 3a to QC 3b is lower with 91%. No thermal cycloreversion of the quadricyclanes 2b and 3b was observed at room temperature within a period of one month. Obviously, a cyano as well as a neighbouring ethynyl substituent are necessary to induce the back-isomerisation at ambient conditions

• switching between the norbornadiene and quadricyclane isomers with two different wavelengths was investigated. Norbornadienes 1 and 2 are quantitatively converted to the corresponding quadricyclanes upon irradiation with light of 385 nm. Back-isomerization with 311 nm to the norbornadiene isomer 1a is less